cis-N-propargyl biotin | 1006727-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: cis-N-propargyl biotin
• 英文别名: 5-[(3aS,4S,6aR)-2-oxo-3-prop-2-ynyl-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid
• CAS: 1006727-81-6
• 化学式: C₁₃H₁₈N₂O₃S
• 分子量: 282.364
• InChiKey: HUUPPRSJDUTSMF-NHCYSSNCSA-N

物化性质

• 熔点：
  170-175 °C
• 沸点：
  567.7±45.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  94.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  D-生物素甲酯 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 8.25h， 生成 cis-N-propargyl biotin
  参考文献：
  名称：

  生物素的选择性N-酰化和N-烷基化

  摘要：

  提出了一种简单有效的方法，用于生物素在其3'-氮的选择性酰化和烷基化。

  DOI：

  10.1021/jo201615j

文献信息

• Expanding the Substrate Tolerance of Biotin Ligase through Exploration of Enzymes from Diverse Species
  作者：Sarah A. Slavoff、Irwin Chen、Yoon-Aa Choi、Alice Y. Ting

  DOI：10.1021/ja076655i

  日期：2008.1.30

  Technologies that enable the site-specific conjugation of chemical probes onto proteins are extremely useful for applications in cell biology and proteomics. We cloned, expressed, and purified biotin ligases from nine different species and screened them for the ability to ligate unnatural analogues of biotin onto the human p67 biotin acceptor domain. We discovered that the biotin ligases of Saccharomyces cerevisiae (yeast) and Pyrococcus horikoshii could accept alkyne and azide derivatives of biotin, respectively. HPLC, gel-shift, and mass spectrometry assays confirmed that these ligation reactions were ATP-and enzyme-dependent, as well as site-specific. We used the P. horikoshii-catalyzed azide ligation reaction to site-specifically introduce a phosphine probe onto p67 using the Staudinger ligation. These new ligation reactions demonstrate the differential substrate specificities of biotin ligases from different organisms and open the door to novel protein labeling applications.
• [EN] BIOMOLECULAR LABELLING USING MULTIFUNCTIONAL BIOTIN ANALOGUES<br/>[FR] MARQUAGE BIOMOLÉCULAIRE UTILISANT DES ANALOGUES MULTIFONCTIONNELS DE BIOTINE
  申请人：UNIV NOTTINGHAM

  公开号：WO2010106347A2

  公开（公告）日：2010-09-23

  Novel biotin analogues, such as 2-Azidobiotin, comprising the ureido ring of natural biotin with the thiophene ring, optionally modified, and a modified sidechain having a functional end group, preferably selected from the group consisting of a carboxylic acid, amine, alcohol, thiol, aldehyde and a halide, and at least one bio- orthogonally reactive chemical group located elsewhere in the sidechain. The analogues are used for labelling target structures and biomolecules, such as peptides and proteins in vitro or in vivo.
• Selective <i>N</i>-Acylation and <i>N</i>-Alkylation of Biotin
  作者：Ashok D. Pehere、Andrew D. Abell

  DOI：10.1021/jo201615j

  日期：2011.11.18

  Simple and efficient methodology is presented for the selective acylation and alkylation of biotin at its 3′-nitrogen.

  提出了一种简单有效的方法，用于生物素在其3'-氮的选择性酰化和烷基化。